Luxury Cabins, Chalets, and Homes on Airbnb in Wisconsin!
Wisconsin is often overlooked in travel media as an exciting destination, which we find to be unfortunate. You don’t often hear people saying “I can’t wait to take an awesome vacation to Wisconsin!” But we know, those people don’t know what they are missing. Wisconsin is a fantastic state to visit for many reasons! There truly is something for everyone! Whether you are looking to explore the picturesque waterfronts of Door County, enjoy the nostalgia of the Wisconsin Dells, indulge in some of the world’s best cheese, or raft, hike, or fish in a beautiful state park, there is definitely some fun to be found in the Badger State.
We think one of the best ways to explore Wisconsin is from a rustic Midwest cabin, a stunning modern, lakefront house, or a cozy and sleek chalet. Wisconsin definitely has many luxury vacation rentals to choose from, and we have listed some of our favorites here. Scroll down below to see some photos and a short description of each rental. There are 16 total cabins, so if you are looking for a specific one, keep scrolling until you reach it! In each description, you will find a link to take you directly to the listing, where you can see more photos and availability, or message the host! If these are a little too luxurious, check out our other list of rentals in Wisconsin, for a more modest budget here!
Walker’s Point - Renovated on HGTV
Milwaukee, Wisconsin. 3 Bedrooms, 2 Bathrooms, Sleeps 8.
If you love HGTV like we do, then you will LOVE this space – it was renovated for an HGTV pilot and is the perfect place for a girl’s getaway, family gathering or even wedding parties! The inside of the home is airy, beautiful and filled with unique designs. The outside has an amazing fenced in backyard oasis with beautiful porch seating, string lights, a grill, and hammock – you can even bring your fur babies! Walkers point is only a few blocks from local restaurants, bars, and wedding venues. Check out this link for more photos and availability of this renovated beauty!
Starlight Tower Manor
Fort Atkinson, Wisconsin. 8 Bedrooms, 3 Bathrooms, Sleeps up to 22.
This 8000 square foot manor has all you and your family need for an epic family vacation to Wisconsin. The manor is perched atop the rolling hills and includes an amazing lookout tower complete with telescopes. The Skylight is also complete with vintage arcade, a bar, and a complete game room so the fun will never stop. We cannot take our eyes off the amazing spiral staircase you will notice as soon as you walk in. When you stay at Starlight, spend your days exploring the Bark River Nature Area, Waterskiing, or ATV riding in the summer and snowmobiling or ice fishing in the winter. At night, go ahead and plan to relax in the movie theater - which can seat up to 35! Check out this link for more photos and availability of the Starlight Manor!
Stunning Waterfront Cabin
Sturgeon Bay, Wisconsin. 3 Bedrooms, 2 Bathrooms, Sleeps 6.
Nestled along the shores of Riley's Bay, a mere 15-minute drive from Sturgeon Bay, this exquisite residence boasts some of the most captivating west-facing sunset views in the area. Featuring a private dock, you and your group can indulge in fishing, swimming, or venture out with the kayaks to explore the beauty of Riley's Bay. Enjoy the tranquility of this home, strategically situated just a short drive from town, providing a perfect balance of peaceful seclusion and easy access to the popular attractions that Door County has to offer. Check out this link to find more photos and availability of this chic lakefront house!
Large Manor with Indoor Pool
Two Rivers, Wisconsin. 4 Bedrooms, 4.5 Bathrooms, Sleeps 10.
Wow - this place looks incredible! This epic vacation rental just screams LUXURY. Beyond the amazing indoor pool complex, complete with not only the indoor pool, but spa, hot tub, and tiki bar, there are 7 high end TVs, a full surround sound system great for movies, three bars, a yoga studio, a family arcade and ping pong table, a fire pit, and even a Peloton. If you can bring yourself to leave this incredible home, Point Beach State Park is right next door and you are less than 40 minutes away from Door County. Check out this link to see more photos and availability of this stunning home!
Cranberry Castle in Northern Wisconsin
Eagle River, Wisconsin. 6 Bedrooms, 5 Bathrooms, Sleeps 15.
The “Castle” is truly high end with no expense spared. The vaulted ceilings and towering lakeside windows provide beautiful views. The main chef's kitchen is fully furnished should you choose not to take your boat out to dinner. There is also a guest kitchen upstairs complete with a stove, oven, microwave and full fridge/freezer should you need more space. The master bedroom sits in the upper south tower with vaulted ceilings and gorgeous lake views. The grand patio offers two full deep seating sets with seating for ten, a full stone outdoor fireplace, built in stainless steel natural gas grill, charcoal Weber and speakers running off the house stereo. Other features include an open floor plan, carved pool table with ample seating, bumper pool table, Yamaha grand piano, beautiful stone fireplace, big screen HDTV and a full size pull out sleeper sofa! One of the coolest features of this house, which truly makes it worth seeking out, is an iPod power stereo system that extends throughout the entire house! Click this link to see more photos and availability of Cranberry Castle!
The Nest in Downtown Lake Geneva
Lake Geneva, Wisconsin. 3 Bedrooms, 1 Bathrooms, Sleeps 8.
This adorable little apartment in downtown Lake Geneva from Keefe Vacation Rentals would make such a fun escape for a bachelorette party or girls weekend! The motto here is "Birds of a feather flock together” and we can definitely see the bird motif throughout. Anchored by a literal nest (swinging trampoline bed), there is so much fun bird imagery in this renovated apartment including an owl bedroom, a flamingo bedroom, and the peacock bedroom! There is a full bathroom and an additional get-ready station for the mornings. Walk right out the door on foot to experience Lake Geneva's nightlife, dining and shopping before heading back to your private nest! Click this link to see more photos and availability of the Nest!
Brand New Cabin on the water with Awesome Views
Portage, Wisconsin. 3 Bedrooms, 3 Bathrooms, Sleeps 8.
This cabin is downright SLEEK. I could spend forever chilling on that sectional in the screened in porch with a nice glass of wine. You can reconnect with nature in this beautiful modern cabin, that is tucked away on 2 private acres overlooking the Wisconsin River! Located close to Devil's Lake, the Wisconsin Dells, and Cascade ski resorts, this modern cabins is the perfect place to unwind and relax with your family! The three bedrooms are set up as one king, one queen, and four bunk beds - each with an ensuite bathroom! Enjoy camp fires around the Solo Stove, and watch the sun set over the tree line. Click this link for more photos and availability of this modern cabin on the river!
Pine Dunes Cabin
Oostburg, Wisconsin. 4 Bedrooms, 3 Bathrooms, Sleeps 10.
This amazing cabin looks like the perfect place to relax along the shores of Lake Michigan! There are so many spaces outside to sit and relax after a great day of exploring the area, you can even hear the sounds of the water! Inside, the floor plan offers plenty of space to relax and hang out, there is room for the entire family. The highlight for us definitely has to be the fire pit and twinkle lights. It looks like an incredibly cozy place to curl up with a glass of wine. You aren’t far from the gem that is Sheboygan, but there is an epic kitchen if you feel like just making meals in the cabin. There is even a great four seasons room for enjoying that morning coffee! Check out this link to find more photos and availability of Pine Dunes cabin!
Beautiful Lakefront Home on Lake Michigan
Newton, Wisconsin. 9 Bedrooms, 6 Bathrooms, Sleeps 16.
This gorgeous vacation rental is spread out over 10,000 square feet, so you and your group will have plenty of room to roam! It boasts so many amenities like an indoor basketball court, an epic pool, a movie theater, pub bar, tennis court, and so much more. You don’t see indoor basketball courts in everyday vacation rentals! We just love the huge picture window that overlooks Lake Michigan. This would make a great option for a small family wedding or even that special event you have been planning. One reviewer found it incredible for his UFC viewing party. Check out this link to find more photos and availability of this gem!
If you think this place looks awesome, check out our list of epic vacation rentals for large families!
Beautiful Hayward Retreat
Hayward, Wisconsin. 3 Bedrooms, 2 Bathrooms, Sleeps 6.
This place is so beautiful, we can’t decide if we like the windows or the beams more?! The cabin is well appointed with many modern amenities and comforts to maximize your enjoyment. After your outdoor adventure, relax in the 3 season porch or outdoor patio with a book or board game, watch a movie, take a soak in the tub, or build a fire in the back-yard fire pit and look at the stars. The beauty won’t be the only thing you love about this cabin. Its location is also perfect; tucked away on 5 wooded acres with direct access to the Birkie/CAMBA trails, but still less than 5 - 10 minutes away from major lake chains, boat docks, and swimming beaches. Click this link to see more photos and availability of this stunning Hayward cabin!
Lakefront Haven
Birchwood, Wisconsin. 3 Bedrooms, 2 Bathrooms, Sleeps 8.
Experience lakeside living with breathtaking views overlooking Big Lake Chetac! Relax in the hot tub, enjoy outdoor movie nights under the stars, and unwind on the deck while grilling up delicious meals. Fish directly from the shore or explore the lake with included kayaks for endless adventures. Nearby, discover ATV and snowmobile trails less than a mile away, as well as a public boat launch with dock parking at the home. With five restaurants, a sandbar, and a public beach accessible by boat, your lakeside getaway promises unforgettable memories. Check out this link to find more photos and availability of this Lakefront Haven!
The Sandwood Cottage
Oostburg, Wisconsin. 4 bedrooms, 2.5 Bathrooms, Sleeps 10.
Welcome to The Sandwood Cottage, where family and friends come together to create cherished memories. Recently remodeled in 2023 and professionally designed by Jordan Gottsacker of Honey and Ace, this cottage is the perfect setting for relaxation and connection. Just 500 feet from the shores of Lake Michigan, the cottage offers endless entertainment. Inside, modern amenities and stylish decor await, including an arcade and Ping-Pong table, 55” Smart HDTVs, high-speed Starlink WiFi, a wood-burning fireplace, and luxurious furnishings. The fully equipped kitchen features quartz countertops, high-end appliances, and a dining area with wooded views. Additional amenities include beach chairs, sand toys, a Weber grill, and a Keurig coffee maker. Check out this link to find more photos and availability of the Sandwood Cottage!
The Lodge
Sturgeon Bay, Wisconsin. 3 Bedrooms, 2.5 Bathrooms, Sleeps 12.
Get ready for the ultimate luxury getaway at The Lodge! Nestled on the picturesque peninsula between Sand Bay and Riley's Bay in Door County, this stunning retreat offers the perfect blend of seclusion and convenience. With modern rustic decor and all the comforts of home, you'll feel right at ease from the moment you arrive. With sleeping arrangements for up to 12 guests and a spacious bar/game room area, there's plenty of space for everyone to unwind and have fun. Don't wait any longer—book your stay today and prepare for an unforgettable vacation filled with cherished memories! Check out this link to find more photos and availability of The Lodge!
Super Fun Door County Family Cabin
Sturgeon Bay, Wisconsin. 4 Bedrooms, 1.5 Bathrooms, Sleeps 8.
Get ready for an unforgettable getaway at this charming waterfront cottage in Door County! Situated just 1-2 miles south of Jacksonport, this location offers easy access to the area's top parks and communities. With 4 bedrooms, outdoor chiminea, 2 fireplaces, and a wheelchair/walker friendly bathroom and bedroom, the hosts have thought of everything to ensure a comfortable stay for the whole family. Plus, Lake Michigan is right outside your front door, providing endless opportunities for outdoor adventures. The main features are thoughtfully designed on the first floor, perfect for bringing everyone together and creating lasting memories. Don't miss out on the chance to experience the beauty and excitement of Door County—book your stay today! Check out this link to find more photos and availability of this super fun Door County Cabin!
Stunning Log Cabin Nestled in the Woods
Wood County, Wisconsin. 5 Bedrooms, 4 Bathrooms, Sleeps 15.
This incredible cabin, called the Gambrel Guesthouse, is a breathtaking escape to the beautiful and peaceful Wisconsin woods. As soon as you pull up, you will immediately fall in love with the front porch, complete with comfy rockers. Inside past the soaring entryway you will be greeted with a cozy space decorated in farmhouse style with real antiques. The gas fore place will keep you warm, the full kitchen will keep you fed, and the dining room is the perfect place to gather as a family. Don’t miss the sauna and pool table! Outside is a griller’s heaven with multiple grills and plenty of places to chill out. Check out this link more photos and availability of the Gambrel Guesthouse here!
Amazing Sunsets in Door County
Bailey’s Harbor. 5 Bedrooms, 4 Bathrooms, Sleeps 15
This beautiful home has amazing sunsets over Kangaroo Lake. Kangaroo lake is an 1100 acre lake in the middle of Door County and 5 minutes from Baileys Harbor, Egg Harbor, Fish Creek and Peninsula state Park! This beautiful home has 110' of water frontage for family fun days on the water. This one is truly for the outdoor lover! Included with the amazing outdoor space is a large outdoor patio, 4 bikes, 3 kayaks, an epic fire pit, a canoe, and a paddleboat! Click this link to review all the photos and amenities this place has to offer!
Epic Luxury Barn
Merrimac, Wisconsin. 5 Bedrooms, 3.5 Bathrooms, Sleeps 12.
No, your eyes are not deceiving you! This barn comes with a beach room, complete with a SAND FLOOR! This epic barn turned vacation rental will surely be the perfect home base for your entire family on vacation! Speaking of family, this place is perfect for kids, and kids at heart (did we mention the catwalk, or slide down into the living room?!) and it’s even pet friendly! This place truly has too many amenities to list but some of our favorites are the 4 person Sauna, 8 person hot tub, swings, and large deck furnished with bar, sectional couch, bean bag chairs and padded chairs, as well as the 3rd floor loft with it’s cozy entertainment space, and 75 inch TV! Click this link to see more photos and availability of this epic barn!
“The Sylvan” at Mill Creek Cabins
Richland Center, Wisconsin. 5 Bedrooms, 3 Bathrooms, Sleeps 10.
The Sylvan Cabin at Mill Creek Cabins, LLC is located on a small lake in the Richland Center area. It is simply breathtaking to behold from the water line! The full kitchen includes a large rustic farm-style table with everything you'll need for a family dinner. The master bedroom is in the loft and features a king-sized bed and a private bathroom. On the main level, there are two queen-sized bedrooms that share the main bathroom. Build a sandcastle, catch some rays on the beach, or take a dip in fresh flowing water! Click this link to see more photos and availability!
Luxury Waterfront Cabin in Door County
Ellison Bay Wisconsin, 4 Bedrooms, 3 Bathrooms Sleeps 6 adults, kids welcome too!
This might take the cake for our favorite luxury rental in Wisconsin. It is so beautiful - from the water views, to the giant windows, and to all the luxury touches, you will find it hard to leave this house! Set on a bluff at the very tip of the Door County Peninsula, Porte Haven feels like you're actually on a boat—that's how close you are to the water. The coolest part of this house is that it was constructed around and old waterside boat house, which now houses a fun hangout entertainment area with a pool table, darts, and more games. The sunroom is the star of the whole house and has a metal roof so rain sounds like pure magic, plus waterproof drapes that allow you to sit out there to watch a storm roll over the lake. You have to browse through all the picture, they are truly spectacular! Check out this link to see more photos and availability of Porte Haven!
Grand View Lakehouse
Eagle River, Wisconsin. 7 Bedrooms, 5 Bathrooms, Sleeps 22.
Grand View is the Lakefront lodge you and your family have been looking for! Inside, you will have almost 5000 square feet to spread out, hang out, and explore. There is an awesome full kitchen on the main level, a wet bar and theater room on the lower level, and several open concept living spaces for every to relax in. Outside there is a private dock, and incredible fire pit, and even a swing set for the kids. We can just imagine relaxing on the big deck and watching the sunsets and sunrises over catfish lake. Check out this link for more photos and availability of Grand View Lakehouse!
There you have it, our list of some of the coolest luxury vacation rentals that we have seen across the state of Wisconsin on Airbnb! Don’t forget to check out our first list of unique places to stay in Wisconsin here. That list features several more budget friendly options.
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Did we miss a great Wisconsin vacation rental? We would love to hear about it! You can reach us via email at seeseeksleep@gmail.com
